The commercial area of Main Street has a characteristic mix of early structures located close to the road and altered later. The now stucco-covered building at 12–14 W. Main is a good example of a mid-nineteenth-century log and frame structure with twentieth-century alterations, such as a neon sign for Main’s Ice Cream and a c. 1930 addition at the rear for an ice cream plant. The Middletown Valley Historical Society (305 W. Main) is quartered in a restored c. 1840 stone three-bay side-hall building. Perhaps the most visually dominant building in Middletown is Zion Lutheran Church (1859; 107 W. Main) built to serve the many German families in the surrounding farms. The massive Greek Revival church was pressed into service as a military hospital in 1862 to 1863.